IE59257B1 - Inorganic acid salt of n-[1(s)-ethoxycarbonyl-3-phenylpropyl]-l-alanylchloride and process for preparing the same - Google Patents

Inorganic acid salt of n-[1(s)-ethoxycarbonyl-3-phenylpropyl]-l-alanylchloride and process for preparing the same

Info

Publication number: IE59257B1
Authority: IE; Ireland
Prior art keywords: acid salt; phenylpropyl; ethoxycarbonyl; inorganic acid; alanylchloride
Prior art date: 1985-08-27

Application number

IE224686A

Other languages

English (en)

Other versions

IE862246L (en

Original Assignee

Kanegafuchi Chemical Ind

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-08-27

Filing date

1986-08-21

Publication date

1994-01-26

1986-08-21 Application filed by Kanegafuchi Chemical Ind filed Critical Kanegafuchi Chemical Ind

1987-02-27 Publication of IE862246L publication Critical patent/IE862246L/en

1994-01-26 Publication of IE59257B1 publication Critical patent/IE59257B1/en

Links

-1 Inorganic acid salt Chemical class 0.000 title claims abstract description 38
IJYLSZDUAYBPCS-AAEUAGOBSA-N ethyl (2s)-2-[[(2s)-1-chloro-1-oxopropan-2-yl]amino]-4-phenylbutanoate Chemical compound CCOC(=O)[C@@H](N[C@@H](C)C(Cl)=O)CCC1=CC=CC=C1 IJYLSZDUAYBPCS-AAEUAGOBSA-N 0.000 title claims abstract description 17
238000004519 manufacturing process Methods 0.000 title claims abstract description 11
CEIWXEQZZZHLDM-AAEUAGOBSA-N (2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoic acid Chemical compound CCOC(=O)[C@@H](N[C@@H](C)C(O)=O)CCC1=CC=CC=C1 CEIWXEQZZZHLDM-AAEUAGOBSA-N 0.000 claims abstract description 17
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims abstract description 12
239000003960 organic solvent Substances 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
150000001875 compounds Chemical class 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
229960003767 alanine Drugs 0.000 description 4
GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 4
150000003839 salts Chemical group 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 3
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000006268 reductive amination reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
WPWUFUBLGADILS-WDSKDSINSA-N Ala-Pro Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O WPWUFUBLGADILS-WDSKDSINSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
229930182821 L-proline Natural products 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
108010087924 alanylproline Proteins 0.000 description 2
150000003862 amino acid derivatives Chemical class 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000007429 general method Methods 0.000 description 2
150000002366 halogen compounds Chemical class 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
229910017053 inorganic salt Inorganic materials 0.000 description 2
229940073584 methylene chloride Drugs 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229950009215 phenylbutanoic acid Drugs 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
229960002429 proline Drugs 0.000 description 2
230000006340 racemization Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JMIPINYUSIWLKU-REOHCLBHSA-N (2s)-2-aminopropanoyl chloride Chemical compound C[C@H](N)C(Cl)=O JMIPINYUSIWLKU-REOHCLBHSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical group CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 description 1
GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical compound CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
108010061435 Enalapril Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
229960000873 enalapril Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000005751 substituted indanyl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Molecular Biology (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IE224686A 1985-08-27 1986-08-21 Inorganic acid salt of n-[1(s)-ethoxycarbonyl-3-phenylpropyl]-l-alanylchloride and process for preparing the same IE59257B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60188242A JPS6248655A (ja)	1985-08-27	1985-08-27	Ｎ−〔１（ｓ）−エトキシカルボニル−３−フエニルプロピル〕−ｌ−アラニルクロリド無機酸塩及びその製造法

Publications (2)

Publication Number	Publication Date
IE862246L IE862246L (en)	1987-02-27
IE59257B1 true IE59257B1 (en)	1994-01-26

Family

ID=16220273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE224686A IE59257B1 (en)	1985-08-27	1986-08-21	Inorganic acid salt of n-[1(s)-ethoxycarbonyl-3-phenylpropyl]-l-alanylchloride and process for preparing the same

Country Status (7)

Country	Link
US (1)	US4760162A (fr)
EP (1)	EP0219651B1 (fr)
JP (1)	JPS6248655A (fr)
CA (1)	CA1261344A (fr)
DE (1)	DE3675328D1 (fr)
ES (1)	ES2000879A6 (fr)
IE (1)	IE59257B1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6300361B1 (en) *	1990-07-25	2001-10-09	Novartis Ag	Stabilized pharmaceutical compositions comprising acid donors
EP2207768A1 (fr) *	2007-11-13	2010-07-21	DSM IP Assets B.V.	Synthèse améliorée du ramipril

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2126180A (en) *	1929-01-16	1938-08-09	Parke Davis & Co	Ureido n-diaryl dicarboxylic acid halides
US2099781A (en) *	1933-10-27	1937-11-23	Du Pont	Halogenation process and product
GB1241844A (en) *	1968-08-23	1971-08-04	Beecham Group Ltd	Penicillins
EP0052094A1 (fr) *	1979-04-25	1982-05-19	BIOCHEMIE Gesellschaft m.b.H.	N-isopropoxycarbonylphénylglycines et leur production
EP0058567B1 (fr) *	1981-02-17	1984-07-25	Warner-Lambert Company	Dérivés acyliques substitués des acides octahydro-1H-isoindole-1-carboxyliques et de ses esters
US4532342A (en) *	1981-02-20	1985-07-30	Warner-Lambert Company	N-substituted amino acids as intermediates in the preparation of acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids
US4556652A (en) *	1984-03-02	1985-12-03	Usv Pharmaceutical Corp.	Antihypertensive spiro-amidoamino compounds
JPS6248696A (ja) *	1985-08-27	1987-03-03	Kanegafuchi Chem Ind Co Ltd	Ｎ−〔１（ｓ）−エトキシカルボニル−３−フエニルプロピル〕−ｌ−アラニル−ｌ−プロリンの製造法

1985
- 1985-08-27 JP JP60188242A patent/JPS6248655A/ja active Granted
1986
- 1986-08-21 CA CA000516506A patent/CA1261344A/fr not_active Expired
- 1986-08-21 IE IE224686A patent/IE59257B1/en not_active IP Right Cessation
- 1986-08-23 DE DE8686111689T patent/DE3675328D1/de not_active Expired - Lifetime
- 1986-08-23 EP EP86111689A patent/EP0219651B1/fr not_active Expired - Lifetime
- 1986-08-25 US US06/900,050 patent/US4760162A/en not_active Expired - Lifetime
- 1986-08-26 ES ES8601352A patent/ES2000879A6/es not_active Expired

Also Published As

Publication number	Publication date
ES2000879A6 (es)	1988-03-16
CA1261344A (fr)	1989-09-26
JPH0333149B2 (fr)	1991-05-16
DE3675328D1 (de)	1990-12-06
IE862246L (en)	1987-02-27
EP0219651A1 (fr)	1987-04-29
EP0219651B1 (fr)	1990-10-31
JPS6248655A (ja)	1987-03-03
US4760162A (en)	1988-07-26

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Date	Code	Title	Description
2006-05-17	MM4A	Patent lapsed

Publication	Publication Date	Title
EP0215335B1 (fr)	1992-11-11	Procédé de préparation de N-[1(S)-éthoxycarbonyl-3-phénylpropyl]-L-alanyl-L-proline
WO1997010197A1 (fr)	1997-03-20	PROCEDE POUR PREPARER DES DERIVES D'ACIDES φ-AMINOALCANOIQUES A PARTIR DE CYCLOALCANONES
EP0098865B1 (fr)	1989-03-01	Synthese de peptides et agents de blocage d'acides amines
JPH07304770A (ja)	1995-11-21	新規ベンゾアゼピノン誘導体
CN1176903C (zh)	2004-11-24	合成n-[(s)-1-羧丁基]-s-丙氨酸酯的方法及其用于合成培哚普利的用途
US6818788B2 (en)	2004-11-16	Method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine esters and use in synthesis of perindopril
US4760162A (en)	1988-07-26	Inorganic acid salt of N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanylchloride and process for preparing the same
US6492541B2 (en)	2002-12-10	Process for the preparation of 3-amino-2-oxo-pyrrolidines, novel intermediates and their use
JPH06145148A (ja)	1994-05-24	新規ベンズアゼピノン誘導体
KR100445124B1 (ko)	2004-11-16	돌라스타틴15의제조방법및그의중간체
AU617197B2 (en)	1991-11-21	Process for the synthesis of optically active aminoacids
CA1298432C (fr)	1992-03-31	PROCEDE POUR LA REPARATION D'.alpha.-L-ASPARTYL-L-PHENYLALANINES A GROUPE N PROTEGE
US6528684B1 (en)	2003-03-04	Synthesis of (R) and (S) -aminocarnitine and their derivatives starting from D- and L-aspartic acid
EA011322B1 (ru)	2009-02-27	Способ получения периндоприла и его солей
EP1513868B1 (fr)	2006-08-09	Procede de production de lisinopril
US6407262B1 (en)	2002-06-18	Process for the preparation of Ramipril
US4508657A (en)	1985-04-02	Peptide synthesis and amino acid blocking agents
PL211506B1 (pl)	2012-05-31	Sposób otrzymywania związków kwasu (2S, 3aS, 7aS)-1-[(S)-alanilo]-oktahydro-1H-indolo-2-karboksylowego i ich zastosowanie w syntezie perindoprilu oraz związek przejściowy
EP0281393B1 (fr)	1993-08-04	Méthode de production de dérivés indaniques
JPWO1999045000A1 (ja)	2002-10-15	４−チアゾリルメチル誘導体の製造方法
SU1241988A3 (ru)	1986-06-30	Способ получени хлоргидрата (2 @ ,3 @ ,7 @ )1- @ 2- @ (1-карбэтокси-3-фенилпропил)амино/-1-оксопропил @ -октагидро-1 @ -индол-2-карбоновой кислоты в виде @ , @ , @ -или @ , @ , @ -изомеров
JPH10291979A (ja)	1998-11-04	１，２，３，４−テトラヒドロイソキノリン−３−カルボン酸ターシャリーブチルアミドの製造方法
KR19990026645A (ko)	1999-04-15	2-[(2,6-디클로로페닐)아미노]페닐아세톡시아세트산의 새로운 제조방법
JPH09255666A (ja)	1997-09-30	ピペラジンアミド化合物及びピペラジンアミド誘導体の製造方法
KR19990065057A (ko)	1999-08-05	아미노산 실릴에스터를 이용한 d-(-)-펜토락톤의 제조방법